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On July 14th, 2010, YouTuber charliezzz uploaded a video titled “The Story of Esteban Winsmore (Episode One),” featuring gameplay footage of a character named Esteban annoying other players in the online virtual world Second Life (shown below). Within the first three years, the video gained over 125,000 views and 125 comments.
On April 24th, 2011, charliezzz released a sequel episode titled “The Story of Esteban Winsmore (Episode Two)” (shown below, left), receiving upwards of 190,000 views and 890 comments in the following two years. On February 11th, 2013, the /r/clubesteban subreddit was created for Esteban Winsmore-related discussions, accumulating upwards of 5,100 subscribers in the following five months. On February 15th, charliezzz uploaded the third episode of the series, in which Winsmore tries to grief players in several locations throughout the Second Life universe (shown below, right). That same day, Redditor charlieso submitted the video to the /r/cringesubreddit, accumulating more than 1,200 up votes and 270 comments in the next five months.
On March 1st, a Facebook page titled “Esteban Winsmore” was launched. On March 26th, NeoGAF member Drencrom submitted a thread linking to several Esteban Winsmore videos, to which other users responded by comparing the character to Ralph Pootawn. On March 20th, charliezzz uploaded the pilot episode of a new series titled “Esteban Winsmore’s Big Furry Adventure,” in which Winsmore interacts with furry players dressed in anthropomorphic animal avatars (shown below). The same day, the video was posted to the /r/cringe subreddit by Redditor WildWildCat. In the first five months, the video received upwards of 160,000 views and the Reddit post garnered more than 1,100 up votes.
On June 10th, charliezzz uploaded a pilot episode for a series titled “The Home Invasions of Esteban Winsmore,” in which the Winsmore griefs players inside their private homes (shown below). The following day, the Internet news site BoingBoing highlighted the video and it was submitted to the /r/cringe subreddit, where it received over 2,600 up votes and 360 comments in the first two months.
Charliezzz has uploaded other griefing videos featuring the character Chargglez Firecaster, who attempts to annoy Second Life players in a similar vein to Winsmore.